Blake Roberts, a man in his mid-50s, carries the scars of significant trauma from the 1990s, leading him to withdraw from much of society. As he stands by the window overlooking Big Bear Lake, a mix of excitement and trepidation fills him with anticipation of Ivy Vandermark's arrival, his best friend's twin sister. Ivy's daughter, Jillian, seeks to write a book about the turbulent events of Blake's youth. Despite the smiles brought about by reminiscing, Blake is wary of revealing the deep wounds and pain he endured.
Over several days, through multiple glasses of wine and cups of coffee, Jillian digs into Blake's past, unearthing the story of his and Logan's move from Boston to Los Angeles. Their conversations, tinged with nostalgia, cover Blake's strained relationship with his father and Hollywood dreams, leading to unforeseen twists, complicated relationships, and the harsh realities of predatory adults preying on young beauty and optimism. As the discussions evolve, Jillian uncovers the depths of Blake's hurt and anger, revealing a downward spiral of self-destructive behaviors and moral dilemmas that shattered his faith in humanity. Amidst these shared reactions and poignant memories, secrets are unveiled, weaving a tale of loyalty and resilience that grips the heart.